1785-86 James Mitchell, Head Master
For information on Mitchell see:
Tangled Roots & Trees Blog entry
Wright, John D. Transylvania, Tutor to the West. Lexington, Ky: University Press of Kentucky, 1980. p. 12
1788-89 Elias Jones, Head Master
1789-91 Isaac Wilson, Head Master

1791-93 James Moore, Head Master
1793-94 James Moore, Acting President

1794-96 Harry Toulmin, First Official President
1796-99 James Moore, President

1799-1804 James Moore, President

1804-1816(?) James Blythe, Acting President

1818-1827 Horace Holley, President
Article on Holley from Wikipedia

1828-1831 Alva Woods, President
1831-1833 John [Mansfield] Lutz, Acting President
1833-1834 Benjamin Orr Peers, Acting President
1834-1835 John [Mansfield] Lutz, Acting President

1835-1837 Thomas Coit, President
1838-1839 Louis Marshall, President

1840-1842 Robert Davidson, President

1842-1849 Henry B. Bascom, President
1849-1856 James B. Dodd, President

1856-1858 Lewis Warner Green, President
Transylvania Preparatory School (High School) 1858 – 1865
1858-1861 Abraham Drake, Principal
1861-1865 James Kennedy Patterson, Principal
Kentucky University at Harrodsburg 1859-1864

1859-1865 Robert Milligan, President
see 1899 yearbook

1865-1878 John Bryan Bowman, Regent
Article from Kentucky Encyclopedia
see 1899 yearbook

1878-1881 Henry Hall White, President
see 1899 yearbook

1881-1897 Charles Louis Loos, President
see 1897, 1906 yearbooks

1897-1900 Reuben L. Cave, President
see 1898 yearbook
1900-1901 Alexander Reed Milligan, Acting President

1901-1906 Burris A. Jenkins, President
see 1902 yearbook

1906-1908 Thomas Benton McCartney, Acting President
see 1907, 1930 yearbooks

1908-1921 Richard Henry Crossfield, President
See also 1920 yearbook.
1921-1922 Thomas Benton McCartney, Acting President

1922-1928 Andrew Davidson Harmon, President

1928-1929 Thomas Benton McCartney, Acting President
see 1907, 1930 yearbooks

1929-1930 Elmer Grant Campbell, Acting President
see 1930 yearbook

1930-1938 Arthur Braden, President
see 1938 yearbook

1938-1939 Richard Henry Crossfield, Interim President

1939-1943 Raymond F. McLain, President
see 1940 yearbook

1943-1945 Leland A. Brown, Acting President
see 1944 yearbook

1946-1951 Raymond F. McLain, President

1951-1957 Frank A. Rose, President

1958-1976 Irvin E. Lunger, President
see 1959 yearbook

1976-1981 William W. Kelly, President
see 1977 yearbook
1981-1982 Irvin E. Lunger, Interim President

1982-1983 David G. Brown, President

1983-2010 Charles L. Shearer, President

8/1/2010-6/30/2014 R. Owen Williams, President

7/1/2014-8/2/2019 Seamus Carey, President

8/15/2019-6/30/2020 John N. Williams, President

7/1/2020-present Brien Lewis, President